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IL302385B2 - Anhydrous compositions of mtor inhibitors and methods of use - Google Patents
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IL302385B2 - Anhydrous compositions of mtor inhibitors and methods of use - Google Patents

Anhydrous compositions of mtor inhibitors and methods of use

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Publication number
IL302385B2
IL302385B2 IL302385A IL30238523A IL302385B2 IL 302385 B2 IL302385 B2 IL 302385B2 IL 302385 A IL302385 A IL 302385A IL 30238523 A IL30238523 A IL 30238523A IL 302385 B2 IL302385 B2 IL 302385B2
Authority
IL
Israel
Prior art keywords
composition
syndrome
tinea
anhydrous gel
total weight
Prior art date
Application number
IL302385A
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Hebrew (he)
Other versions
IL302385B1 (en
IL302385A (en
Original Assignee
Palvella Therapeutics Inc
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Publication date
Application filed by Palvella Therapeutics Inc filed Critical Palvella Therapeutics Inc
Publication of IL302385A publication Critical patent/IL302385A/en
Publication of IL302385B1 publication Critical patent/IL302385B1/en
Publication of IL302385B2 publication Critical patent/IL302385B2/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/436—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Dermatology (AREA)
  • Inorganic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

Divisional application of 267869/2 ANHYDROUS COMPOSITIONS OF mTOR INHIBITORS AND METHODS OF USE This application is a division of co-pending application No. IL 267869.
PRIORITY PARAGRAPH id="p-1" id="p-1" id="p-1" id="p-1" id="p-1" id="p-1"
[0001]This application claims priority to the U.S. Provisional Application No. 62/443,117, filed on January 6, 2017 , titled "Anhydrous compositions of mTOR inhibitors and methods of use", which is incorporated herein by reference.
SUMMARY id="p-2" id="p-2" id="p-2" id="p-2" id="p-2" id="p-2"
[0002]Disclosed herein are compositions and methods for topical delivery of mTOR inhibitors. In one embodiment, an anhydrous composition comprises an effective amount of one or more mTOR inhibitors, one or more solvents, one or more gelling agents, and one or more antioxidants. In some embodiments, the mTOR inhibitor is present from about 0.1 wt% to about 20 wt% of the total composition. In some embodiments, the solvent is present from about 1 wt% to about 99.9 wt% of the total composition. In some embodiments, the gelling agent is present from about 0.1 wt% to about 5 wt% of the total composition. In some embodiments, the antioxidant is present from about 0.001 wt% to about 1 wt% of the total composition. id="p-3" id="p-3" id="p-3" id="p-3" id="p-3" id="p-3"
[0003]In additional embodiments, methods of treating a skin disorder in a subject in need thereof comprises topically administering an effective amount of an anhydrous composition comprising an effective amount of one or more mTOR inhibitors, one or more solvents, one or more gelling agents, and one or more antioxidants. In some embodiments, the mTOR inhibitor is present from about 0.1 wt% to about 20 wt% of the total composition. In some embodiments, the solvent is present from about 1 wt% to about 99.9 wt% of the total composition. In some embodiments, the gelling agent is present from about 0.1 wt% to about wt% of the total composition. In some embodiments, the antioxidant is present from about 0.001 wt% to about 1 wt% of the total composition.
BRIEF DESCRIPTION OF FIGURES id="p-4" id="p-4" id="p-4" id="p-4" id="p-4" id="p-4"
[0004]FIG. 1 depicts total mean deposition of rapamycin (ng) in the tissue (combined epidermis and dermis) following application of rapamycin compositions (03, NA21, NA22, NA23, NA17, NA19, NA25, AG14, NA 26, NA24, TD201). Each error bar is determined using 1 standard deviation from the mean (n=5).

Claims (13)

Divisional application of 267869/ - 37 - CLAIMS What Is Claimed Is:
1. A topical anhydrous gel composition for use in the treatment of a skin disorder, wherein the topical anhydrous gel composition comprises: 2.5 wt % to about 4.5 wt % of rapamycin or a pharmaceutically acceptable salt thereof, based upon the total weight of the composition, about 80 wt % to about 97 wt % of a solvent, based upon the total weight of the composition, wherein the solvent is about 1 wt % to about 30 wt % diisopropyl adipate based upon the total weight of the composition, about 1 wt % to about wt % glycerol based upon the total weight of the composition, about 40 wt % to about 60 wt % polyethylene glycol based upon the total weight of the composition, and about 1 wt % to about 30 wt % isopropyl alcohol, based upon the total weight of the composition, about 0.1 wt % to about 5 wt % of a gelling agent, based upon the total weight of the composition, about 0.001 wt % to about 1 wt % of an antioxidant, based upon the total weight of the composition, and optionally an additional pharmaceutically acceptable excipient, wherein a total weight of the composition is 100 wt %, and wherein the topical anhydrous gel composition has a pH of about 4 to about 8.
2. The topical anhydrous gel composition of claim 1, wherein the gelling agent is selected from the group consisting of hydroxypropyl cellulose, carbomer 981, carbomer 934P, glyceryl tris 12-hydroxy stearate, hydroxy stearin, propylene carbonate, polyvinyl pyrrolidine, and combinations thereof.
3. The topical anhydrous gel composition of claim 1, wherein the antioxidant is selected from the group consisting of ascorbyl palmitate, propyl gallate, α-tocopherol, and combinations thereof.
4. The topical anhydrous gel composition of claim 1, wherein the composition further comprises a polymeric surfactant, a moisturizing agent, a cooling agent, a rheology modifier, a preservative, and combinations thereof.
5. The topical anhydrous gel composition of claim 1, wherein the composition further comprises a skin care agent selected from the group consisting of cis- retinoic acid, trans-retinoic acid, retinol, retinyl esters, and combinations thereof. Divisional application of 267869/ - 38 -
6. The topical anhydrous gel composition of claim 1, wherein the composition comprises: rapamycin from about 3 wt % to about 4.5 wt % of the composition; polyethylene glycol from about 40 wt % to about 60 wt % of the composition; isopropyl alcohol at about 15 wt % of the composition; diisopropyl adipate at about 15 wt % of the composition; glycerol at about 10 wt % of the composition; the gelling agent from about 0.1 wt % to about 1 wt % of the composition; the antioxidant from about 0.001 wt % to about 0.1 wt % of the composition; and wherein the additional pharmaceutically acceptable excipient is a buffer.
7. The topical anhydrous gel composition of claim 6, wherein the composition comprises: rapamycin at about 3.9 wt % of the composition; isopropyl alcohol at about 15 wt % of the composition; polyethylene glycol at about 55.3 wt % of the composition; diisopropyl adipate at about 15 wt % of the composition; glycerol at about 10 wt % of the composition; wherein the gelling agent is hydroxypropyl cellulose; wherein the antioxidant is selected from propyl gallate, ascorbyl palmitate, and α-tocopherol; and a buffer.
8. The topical anhydrous gel composition of claim 7, wherein the anhydrous gel composition comprises: rapamycin at about 3.9 wt % of the composition; isopropyl alcohol at about 15 wt % of the composition; polyethylene glycol at about 55.3 wt % of the composition; diisopropyl adipate at about 15 wt % of the composition; glycerol at about 10 wt % of the composition; Divisional application of 267869/ - 39 - hydroxypropyl cellulose at about 0.75 wt % of the composition; propyl gallate at about 0.05 wt % of the composition; ascorbyl palmitate at about 0.02 wt % of the composition; α-tocopherol at about 0.002 wt % of the composition; and a buffer.
9. The topical anhydrous gel composition of claim 1, wherein the composition has a pH of about 4.5 to about 6.
10. The topical anhydrous gel composition of claim 1, wherein the composition has a viscosity of about 5000 cP to about 20,000 cP.
11. The topical anhydrous gel composition of claim 1, wherein the rapamycin or pharmaceutically acceptable salt thereof is stable in the composition at a temperature of about 4 °C to about 40 °C for a period of 12 to 36 months.
12. The topical anhydrous gel composition of claim 1, wherein the skin disorder is selected from the group consisting of plantar hyperkeratosis, blisters, tuberous sclerosis, seborrheic keratosis, keratosis pilaris, epidermolysis bullosa, multiple minute digitate hyperkeratosis, hyperkeratosis lenticularis perstans, stasis dermatitis, focal acral hyperkeratosis, follicular hyperkeratosis, lichenoid keratoses, lichen planus, lichen sclerosus, chronic erosive oral lichen, Conradi-Eltinermann, epidermolytic ichthyosis, erythrokeratoderma variabilis, ichthyosis hystrix, KID syndrome, Netherton syndrome, Olmsted syndrome, Refsum disease, Sjogren-Larsson Syndrome, actinic keratosis, pachyonychia congenita, hyperhidrosis, warts, calluses, dermatitis, contact dermatitis, drug-induced dermatitis, allergic dermatitis, nummular dermatitis, perioral dermatitis, neurodermatitis, seborrheic dermatitis, atopic dermatitis, psoriasis, acne, carbunculosis, cellulitis, furunculosis, granuloma, acanthosis nigricans, athlete's foot, bacterial vaginosis, balanitis, dermatofibrosarcoma protruberans, basal cell carcinoma, squamous cell carcinoma, melanoma, merkel cell carcinoma, keloid, cystic lymphangioma, Cavernous lymphangioma, venous malformation, epidermal nevi, bromhidrosis, dermatophytosis, candidiasis, onychomycosis, tinea, tinea alba, tinea pedis, tinea unguium, tinea manuum, tinea cruris, tinea corporis, tinea capitis, tinea faciei, tinea barbae, tinea imbricata, tinea nigra, tinea versicolor, tinea incognito, eczema, dyshydrotic eczema, decubitous ulcer, ecthyma, erysipalus, erythema multiforme, impetigo, insect bites, genital warts, hemangioma, herpes, hives, hyperhidrosis, filariasis, lentigines, lupus, miliaria, milker's nodules, molluscum contagiosum, myiasis, scabies, cutaneous larva migrans, furuncular myiasis, migratory myiasis, pediculosis, nevus araneus, panniculitis, paronychia, pemphigoid, pityriasis, pruritis vulvae, rosacea, trichomoniasis, vaginal yeast infection, vitiligo, xeroderma, angiofibroma, Bannayan-Riley-Ruvalcaba syndrome, basal cell nevus syndrome, Birt-Hogg-Dube syndrome, Blue rubber bleb nevus syndrome, Cowden Divisional application of 267869/ - 40 - disease, cutaneous T-cell lymphoma, diffuse microcystic lymphatic malformations, epidermolysis bullosa simplex, extramammary paget, familial multiple discoid fibromas, Hailey-Hailey disease, infantile hemangiomas, juvenile polyposis syndrome, Kaposi sarcoma, Kaposiform hemangioendothelioma, Keloid scar disease, Lhermitte-Duclos syndrome, metastatic melanoma, Muir-Torre syndrome, neurofibromatosis, nonmelanoma skin cancer, oral graft-versus-host disease, Pemphigus vulgaris, Peutz-Jeghers syndrome, Port-wine stains, Proteus syndrome, Proteus-like Syndrome, refractory hemangioendotheliomas in Maffucci syndrome, Sturge-weber syndrome, hereditary footpad hyperkeratosis (HFH) in canines, cutaneous sarcoidosis, cutaneous Castleman Disease, Bullous Pemphigoid, and combinations thereof.
13. The topical anhydrous gel composition of claim 12, wherein the skin disorder is selected from the group consisting of pachyonychia congenita, basal cell nevus syndrome, angiofibroma, diffuse microcystic lymphatic malformations, and epidermolysis bullosa simplex. For the Applicant Naschitz, Brandes Amir & Co. P-15975-IL1
IL302385A 2017-01-06 2018-01-05 Anhydrous compositions of mtor inhibitors and methods of use IL302385B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201762443117P 2017-01-06 2017-01-06
PCT/US2018/012647 WO2018129364A1 (en) 2017-01-06 2018-01-05 Anhydrous compositions of mtor inhibitors and methods of use

Publications (3)

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IL302385A IL302385A (en) 2023-06-01
IL302385B1 IL302385B1 (en) 2024-02-01
IL302385B2 true IL302385B2 (en) 2024-06-01

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IL302385A IL302385B2 (en) 2017-01-06 2018-01-05 Anhydrous compositions of mtor inhibitors and methods of use
IL267869A IL267869B2 (en) 2017-01-06 2018-01-05 Anhydrous compositions of mtor inhibitors and methods of use

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US (4) US10722499B2 (en)
EP (1) EP3565520B1 (en)
JP (3) JP7108631B2 (en)
CN (1) CN110520097B (en)
AU (2) AU2018205253B2 (en)
CA (1) CA3049402A1 (en)
DK (1) DK3565520T3 (en)
ES (1) ES3064393T3 (en)
FI (1) FI3565520T3 (en)
IL (2) IL302385B2 (en)
PT (1) PT3565520T (en)
WO (1) WO2018129364A1 (en)

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